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Chapter 19: Q70 (page 763)

Although p-hydroxybenzoic acid is less acidic than benzoic acid, o-hydroxybenzoic acid is slightly more acidic than benzoic acid. Explain this result.

Short Answer

Expert verified

This occurs due to the stabilization of carbanion.

Step by step solution

01

p-hydroxybenzoic acid

The p-hydroxybenzoic acid is less acidic than benzoic acid. It has an alcohol group at para position to the acidic group of the benzoic acid. Theresonance effect destabilizes the conjugate base.

02

Step 2: o-hydroxybenzoic acid

The o-hydroxybenzoic acid is more acidic than benzoic acid.It has an alcohol group at ortho position to the acidic group of the benzoic acid.

03

Explanation

The p-hydroxybenzoic acid hasan OH group, whichdonates electron density by its resonance effect, destabilizing the conjugate base and making the acid less acidic than benzoic acid.

Destabilized conjugate base

The o-hydroxybenzoic acid has intramolecular hydrogen bonding, stabilizing the conjugate base and making the compound more acidic than benzoic acid.

Stabilized conjugate base

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Most popular questions from this chapter

Threonine is a naturally occurring amino acid that has two stereogenic centers.

a. Draw the four possible stereoisomers using wedges and dashes.

b. The naturally occurring amino acid has the 2S,3R configuration at its two stereogenic centers. Which structure does this correspond to?

Because phenol $(C_{6} H_{5} OH)$ is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base ${NaHCO}_{3}$ . Using this information, write out an extraction sequence that can be used to separate $(C_{6} H_{5} OH)$ , benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.

Question: Match each of the following ${pk}_{a}$ values (3.2, 4.9, and 0.2) to the appropriate carboxylic acid:

(a) ${CH}_{3} {CH}_{2} COOH; [b] {CF}_{3} COOH; [c] {ICH}_{2} COOH$

Although codeine occurs in low concentration in the opium poppy, most of the codeine used in medicine is prepared from morphine (the principal component of opium) by the following reaction. Explain why selective methylation occurs at only OH in morphine to give codeine. Codeine is a less potent and less addictive analgesic than morphine.

morphine codeine

Match the ${}^{13}C$ NMR data to the appropriate structure.

Spectrum [1]: signals at 14, 22, 27, 34, 181 ppm

Spectrum [2]: signals at 27, 39, 186 ppm

Spectrum [3]: signals at 22, 26, 43, 180 ppm

a.

b.

c.

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